Antiseptic soap compositions



United States Patent 2,926,141 ANTISEPTIC SOAP COMPOSITIONS David J. Beaver, Richmond. Heights, Paul J. Stotfel, Florissant, and Roland S.'Shumard, Brentwood, Mo., assignors to Monsanto Chemical Company, St. Louis, Mo., a corporation of Delaware No Drawing. Application June 22, 1953 Serial No. 363,382 Claims. (Cl. 252-107) This invention relates to new and novel detergent compositions. More particularly it relates to detergent compositions exhibiting antiseptic properties. Still more particularly it relates to antiseptic detergent compositions containing a trihalogenated tris-phenol.

In accordance with this invention it has been found that trihalogenated tris-phenols of the general formula where X X and X are like or unlike halogen atoms and their mono-alkali metal salts exhibit antiseptic properties in a detergent composition when present in minor proportions. The new antiseptic agents of this invention are easily incorporated in detergent compositions whether the latter be solid or liquid. They are non-volatile and remain permanently in the detergent composition. They do not effect the lathering, cleansing, or physical properties of the detergent composition and neither do they impart an unpleasant odor nor discolor the finished detergent composition.

As exemplary of this invention several halogenated trisphenols were compared in a detergent composition and compared to detergent compositions containing analogous halogenated tris-phenols. The halogenated tris-phenols listed below are, respectively incorporated in an Ivory brand neutral white high grade toilet soap (a mixture of 80% sodium soap and 20% potassium soap produced from a 70% tallow and 30% coconut oil glycerine blend in accordance with US. 2,295,594) to form 2% by weight halogenated tris-phenol detergent compositions, that is a ratio one part halogenated tris-phenol to 49 parts soap. Aliquots of each are added to a nutrient agar medium so as to give concentrations of 0.67 p.p.m., 1.25 p.p.m., 2.5 p.p.m. and 5 p.p.m. of the respective halogenated tris-phenols in the nutrient agar. The agar, in each case, is then poured into a petri dish, allowed to harden, and then streaked with a 24 hour old culture of Mimrococcus pyrogenes var. aureus (formerly known as Staphylococcus aureus) of standard resistance. The incubation in each case was made at 37 C. for 48 hours and the degree of growth noted. The results are tabulated below:

Legend:

No growth. 2-+ Extremely light growth. Very light growth.

might to moderate growth.

Normal heavy growth.

Patented Feb. 23, 1960 ICC By replacing any one of the aforementioned halogenated tris-phenols of the aforedescribed detergent compositions with an equal weight of 4-bromo-a ,a -bis(S-bromo-Z- hydroxy-phenyl)-2,6-xyleno1 or 4-chloro a ,a bis(5- bromo-Z-hyrdroxy-phenyl) 2,6 xylenol and similarly evaluating excellent control of Staphylococcus aureus is obtained. Good control of Staphylococci is also obtained employing the mono-alkali metal salts, e.g. mono-sodium salts of the halogenated tris-phenols of this invention.

The tri-halogenated tris-phenol antiseptic agents of this invention are readily prepared by reacting a 2,6-dimethyol-para-halo-phenol with a p-halo-phenol in the presence of a condensation catalyst. For example upon heating in a suitable reaction vessel at about 90 C. a mixture containing about 18.9 parts by weight of 2,6-dimethylol-p-chlorcphenol, about 51.2 parts by weight of p-chlorophenol, and about 4 parts by weight of 37% hydrochloric acid for about one hour, cooling the reaction mix so obtained, adding thereto and intimately mixing about parts by weight of heptane, filtering and recrystallizing from toluene there is obtained 4-ChlO1'0-u ,a bis-(5-chloro-2-hydroxyphenyl)-2,6-xylenol (M.P. about 234 C.) in a 73.5% yield.

The mono-alkali metal salts are conveniently prepared by heating in suitable proportions, i.e. equimolecular proportions, a tri-halogenated tris-phenol of this invention with an aqueous solution of an alkali metal hydroxide such as sodium or potassium hydroxide.

Relatively small amounts of the halogenated trisphenols of this invention or their alkali metal salts or mixtures of said phenols and said alkali metal salts in a detergent composition have been found to yield eflicient antiseptic detergent compositions. Amounts as low as 0.5-1% by weight based upon the detergent of a halogenated tris-phenol of this invention or its alkali metal salt or mixtures thereof have proved satisfactory in some instances. However, it is preferred to employ amounts in the order of 1-3% by weight. While larger amounts can be employed, as for example up to 10% by weight, the upper limit is determined by practical considerations.

The halogenated tris-phenols of this invention or the alkali metal salts thereof or mixtures thereof may be added to the detergent composition in any suitable manner during the crutching or milling or similar operation. The antiseptic agents of this invention may be first dissolved in a suitable solvent and then incorporated in the detergent if so desired. In general any method which results in the halogenated tris-phenols of this invention or their alkali metal salts thereof or mixtures of said phenols and said salts being uniformly incorporated in the final detergent composition is satisfactory.

While the invention has been described relative to several particular embodiments it is not so limited but that many variations and modifications which are obvious to those skilled in the art to which this invention appertains may be made without departing from the spirit or scope of the invention.

What is claimed is:

1. An antiseptic detergent composition consisting essentially of a detergent soap and 0.5 to 10% by'weigh-t based on the detergent soap of a halogenated tris-phenol having the structural formula OH OH where X X and X, are halogen atoms selected from the group consisting of chlorine and bromine.

2; An antiseptiedetergent composition consisting-essentially of :1 detergent soap and about 1%" to 3% by weight tiallysof adetergent soap and about, 1v%,to.3%, by. weight based one detergent soap of 4eChIOI'OY7GKGF-biS(srbl'omOr based on a detergent soap of 4-c111O1'O-a ,a -biS(5- 2-hydroxy-pheny1)-2,6-xyleno1. chloro-Z-hydroxy-phenyl) -2,6-xyleno1.

3. An antiseptic detergentcomposition consjstingessen- 5 References Citedgin thefile of this patent tially of a detergent'soap and about; 1% to 3%. by'weight; UNITED STATES; PATENTSv based on a detergent soap off4-bromoa?,a5-bis(S-chloro: p z hydmxy phenyl) 26 Xylen1 2,638,486 ChlddlX et a1; May 12, 1953 4. An antiseptic detergent composition consisting essentially of a detergent soap and about, 1% to 3% by weight 10 OTHER'REFERENQES based on a detergent soap of 4-bromo-a ,a -bis(5bromor QZE IE-CM I ,.N y: Pages Z-hydroxy-phenyl)-2,6-xylenol.

5. An antiseptic detergent composition consisting essen- 

1. AN ANTISEPTIC DETERGENT COMPOSITION CONSISTING ESSENTIALLY OF A DETERGENT SOAP AND 0.5 TO 10% BY WEIGHT BASED ON THE DETERGENT SOAP OF A HALOGENATED TRIS-PHENOL HAVING THE STRUCTUREAL FORMULA 